Let me put you in my frame of mind: I started going to lunch and decided that I wanted to do something different than my normal food cart or Dunkin' Donuts routine. I ended up at a near-by 'tavern' which I knew had good burgers. When I walked in, I was the only customer there.
I was generally my pleasant self and, while I found the bar-tender attractive, I thought better of trying anything (mostly because I didn't want to come across as annoying or creepy). Some friendly banter occurred, I got a beer and a hamburger, and all was well.
Then, she pauses, looks at me, and says "you look like an honest guy - can I ask you something?" She proceeds to tell me about her situation with her live-in boyfriend and how she's being ignored (the anecdote provided, briefly: "it was my birthday yesterday and he avoided me all day, finally stumbling in drunk and passing out after midnight."). I doled out what I believe is good advice ("if someone isn't making you their priority, don't make them yours") and we had a nice discussion about relationships and friendships.
I'm still trying to wrap my head around the whole thing - I'm most certainly over-thinking it - but it was nice to have the conversation. I feel good for giving good advice, bad for not pursuing, and odd for feeling that these paths feel like they are polar opposites.
In any case, I got a free beer out of it. :)